I picked up a Bareboat from Neilson in Porto Heli last year and sailed across to Hydra (No problem berthing on Key) and then over to the western Cyclades (Kea, Kythnos, Serifos, Sifnos,Milos) then back over to the Pelopenese for a few days before sailing back to Porto Heli. The bus trip from Athens to Porto Heli is a bit of a drag but if you want to stay away from the Athens/Lavrion rush you will find that Milos and the Pelopenese are nice and quiet. Whole trip took 2 weeks and was pretty cheap

I'm also chartering there for the first time and I have two main questions (among the dozens). If I do a one-way from Athens or Lavrio to Paros, would I be able to, with an overnight or long first day and only visiting 4 or 5 islands, sail the southern Cyclades on a one week charter?

Are you familiar with Royal Eagle? They have some fairly new yachts available. Thanks for any suggestions.

The short answer is Yes -depending on your experience, the time of year. and how much "relaxing" you want to do. You should not be doing hardly any up wind sailing in the summer but just remember that this is a popular route and the further you get from Athens the better it gets (If you like it quiet like me). The only real problem you need to be careful of is if you are doing the return trip which can be against a strong wind.

Not much to add! Sailing off from Lavrion will save you one day that you can spend on an island of your choice. The full options are Kea, Kythnos, Serifos, Syros, Mykonos, Rinia (offshore anchorage), Sifnos and Naoussa Paros. Sailing further south may pose problems when beating back to North.

Maybe that is old post, but that is nice Trip... Royal Eagle have new yachts now model 2014/15, just if you reserve yacht from German Royal Eagle maybe you take better price.
Also i think that if you choose to start your holidays from Athens (12:00 - 13:30) then you can receive your boat earlier than Lavrion (17:00). Ask them for it...

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